Week 3 of “Dear Skylar!” Remember you can submit your own questions by click here.
Question 1
Dear Skylar, What puts you in the mood and mind set to want to use a Strap-on on a male sub? And can you get off using a Strap-on?
Signed, Strap-on Fan
Answer
Hello Strap-on Fan!!!! This Goddess loves anal play!! I can’t live without being able to play with a guy’s ass. That being said, my favorite way to penetrate him is with my fingers. I find it more intimate when I feel you and you feel me, body part to body part, so to speak. Not to mention I can feel what’s going on and adjust my fuckery accordingly.
I use a strap-on as well, but for more of a “down and dirty” type of experience when I really want you to feel like I have “mounted” you. What puts me in the mindset to use a strap-on?Sometimes I will do so if I feel you have been a little bit naughty, sometimes I want to watch your reaction to being pounded and other times, I just feel like it. Gemini Goddess remember? lol
When it comes to getting off, I will say it’s not the norm for me while using a strap-on but have had it happen on several occasions. Sometimes you get things just right. lol
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Question 2
Dear Skylar, I’m always able to call a lovely lady at LDW, do you have any masturbation games you recommend I can play to prolong my stroking session?
Signed, A different kind of Gamer
Answer
Dear Gamer, there are soooo many wonderful stroking games to indulge in but my favorite involve two decks of cards and a set of rules. I call it “Pleasure Deck.” In this game card denote different things the masturbator MUST do and is very much a game of chance. I shuffle the cards and for every card I pull, you will have to perform a task. Here they are:
Queen – Pinch a nipple as hard as you can.
King -Masturbate with your non-dominate hand for 5 min straight while I tease you.
Ace- Push an object into your asshole.
Jack – Play with your balls for 2 minutes.
Joker – Hump a pillow for 5 minutes.
2 of Spades – Switch hands.
Now at the end of the call, the Goddess pulls a final card.
If a Red card is pulled, you cum.
If a Black card is pulled, you don’t cum.
If a Red Queen is called, the Goddess tells you where to cum.
I love this game and think it you will find yourself addicted to playing it! lol
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Question 3
Counting down from 5 to 1. One being the Greatest. What are the 5 things that make you horny????
Signed, The Mathematician
Answer:
Dear Mathematician,
Wow this question really made me think. lol. So without further ado here is my 1-5.
5. Watching a guy slowly strip for me
4. Fucking a guys ass with my fingers and hearing him moan.
3. A sub giving me a full erotic body massage.
2. Tying you up and playing with your body at will.
1. You flat on your back, me riding your lips and tongue.
I hope you took notes. You’re welcome. lol
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Question 4
Dear Skylar, What is your favorite way to discreetly (or maybe not so discreetly) find out how big a guy’s cock is?
Signed Asking for a Friend.
Answer
Dear “Asking for a Friend,”
I simply tell him to drop his pants and show me. I find that. works best for me.
Question 5
Dear Skylar, Your male sex slave has not been following order as he should, and he has been breaking your house rules. Next weekend is a 3-day weekend and you take Friday off to address the matter. So, adding Friday to the 3-day weekend you now have 4 days to get your slave back on the right track.
By the time Monday night rolls around you will be completely sexually satisfied much like a kitten with a full tummy taking a nap in the sun. Your sex slave on the other hand is left physically and emotionally broken trapped in a dark room not able to complete a single thought as he sits or lies there in his own flop sweat.
My question is what would your agenda be for this pleasure for you/pain for him 4-day weekend?
Signed, “The Rule Breaker”
Answer:
Dear Rule Breaker,
I have taken sometime to think of what my course of action would be. And punishment and denial would be my two top agendas. You would of course, have many chores and tasks around the house to do along with the agenda. So the four days might look like this:
Day 1: Flogging thy ass, put in chastity during day, cock released in the evening and edged for hours, NO cumming. I will ride your mouth to for my pleasure.
Day 2: Flogging thy balls, put in chastity during the day, cock released in the evening and sounded, then edged. No cumming. I will ride your mouth for my pleasure. IcyHot put on the tip of cock right before bed. Sweet dreams.
Day 3: Using a cane on thy ass, put in chastity during the day and all night. Butt plug inserted that morning and left in for 10 hours. I will ride your mouth for my pleasure. IcyHot applied to balls right before you are ordered to sleep on the floor with a pillow and blanket.
Day 4 – Using a flogger every hour on your ass and balls during the day. Locked in chastity day and night. Fucked with an 8 inch strap-on. Then I will tie you up and make you watch me fuck another guy. IcyHot on your asshole right before bed. Night night, sleep tight. And learn to follow rules bitch!
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Question 6
Dear Skylar, If I was a naughty boy how much would you punish me, to make you feel better?
Signed, Naughty Boy
Answer:
Dear Naughty,
Without knowing the crime the naughty boy has committed, it’s hard to give a simple answer to this. What I can say, is that my punishments can be an array of: Flogging, canning, IcyHot, Edging without coming, chastity for days, embarrassing tasks in public, and humiliating tasks in private.
Sometime a punishment comes fast (but you won’t), and sometimes it’s a multi-day experience. Also to keep in mind, I am a Gemini Goddess, so you never know how severe the punishment will be.
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Question 7 :
Dear Skylar, How do I overcome my fear to become more feminine? I keep looking at fake breast silicone body type but I just can’t get over my fear of acceptance.
Signed, Fearful
Answer:
Dear Fearful,
It’s a natural emotion to feel when starting out on this journey. So you are not alone in your feelings. So many experience this. I think there are several things to keep in mind. First, small steps are the key to finding your feminine vibe and where you are comfortable.
Now the one bit of information I don’t have here is if you are married or single. Being married presents challenges as you don’t have the freedom to explore while trying to hide it from your wife. I know many guys have a secret place they stash panties, make-up, nylons, etc. Some even tell me they secretly wear panties to work under their work clothes.
But if you can’t do any form of dressing up, other options are creating a private account on Pinterest or Tumblr and posting pics of fem things you find appealing. Set aside sometime each week to exploring your fem side. Even going through magazines, or online websites.
Connecting to your Fem side can be how you walk, getting a manicure or facial, watching movies you know would appeal to women, reading blocks about others who are on your same journey. There are so many ways to explore.
When it comes to fear of acceptance there is no one size fits all answer, but I can tell you, only you will know when the time is right to share your love of all things feminine. Perhaps exploring on your own is the first step and discovering what you like and enjoy. Never be ashamed of what you are into. We are all unique creatures and our love of kinks and fetishes make up part of who we are. xxx
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Have questions you want to discuss privately during a one on one call?
I am on most nights from 7PM to 1AM EST.
You can find me on www.voxerotic.com
On Skype as : BlueEyedSky Sinclair
Email: Skyar@enchantrixempire.com
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